Total, Asymmetric Synthesis of (+)-Castanospermine, (+)-6-Deoxycastanospermine, and (+)-6-Deoxy-6-fluorocastanospermine

Article abstract of DOI:10.1021/jo00006a031

Bromination of the dibenzyl acetal of (-)-(1S,4S)-7-oxabicyclo<2.2.1>hept-5-en-2-one ((-)-5) led to (+)-(1S,5S,6S,7S)-6-endo-(benzyloxy)-5-exo-bromo-7-oxabicyclo<2.2.1>heptan-2-one (25).Baeyer-Villiger oxidation of 25 gave 2-O-benzyl-3-bromo-3,5-dideoxy-β